


A True Dickotomy

by DevilOfWire



Series: DevilOfWire's Kinktober 2020 [13]
Category: South Park
Genre: Aged-Up Characters, Anal Sex, Body Worship, Bottom Phillip "Pip" Pirrup, Cock Piercing, Crossdressing, Established Relationship, Feminization, Frottage, Humor, Kinktober 2020, M/M, Nipple Piercings, One Shot, Panties, Piercings, Plot What Plot/Porn Without Plot, Size Difference, Smut, Socks, Spanking, Stockings, Thighs, Top Damien Thorn, Wet & Messy
Language: English
Status: Completed
Published: 2020-10-13
Updated: 2020-10-13
Packaged: 2021-03-07 22:01:48
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,193
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26994850
Author URL: https://archiveofourown.org/users/DevilOfWire/pseuds/DevilOfWire
Summary: 13. Body worship | Spanking | FrottageUnder eye makeup and thigh-highs, sometimes even Damien could forget it was a guy he was dating after all.Until it becomes unavoidably obvious—and poking him in the side—that is.
Relationships: Philip "Pip" Pirrip/Damien Thorn
Series: DevilOfWire's Kinktober 2020 [13]
Series URL: https://archiveofourown.org/series/1950421
Comments: 2
Kudos: 58
Collections: Kinktober 2020





	A True Dickotomy

**Author's Note:**

> **IF YOU ARE UNDER 18 DO _NOT_ READ.**
> 
> Soft sequel to last year’s PWP fic! Idek why, I just really like this semi-crack pair I guess lmao 
> 
> And now with the eventual anal which I so desperately wanted to detail last fic—and every fic, tbh—but was too tired to do! Huzzah! :D

Even after having arrived home, Damien still can’t believe it.

“Is something wrong, Damien?” Pip giggles past him, moving briskly to put away the fresh groceries, and then starting on the other, less perishable goods they’d got from general stores.

Damien shakes his head from his stupor, breathing in as he remembers he should be helping him, as well. “Oh, no,” Damien dismisses.

“Really?” Pip tilts his head. “Because I must say, something definitely seems amiss with you, dear. Was it something I did? Or did you forget something again?” he laughs.

“No, nothing like that...” Damien grumbles, awkwardly shifting as they’ve already finished their task. “It’s just... uh...”

“What?” Pip asks, standing with his hands idly to either side.

And that was exactly the thing.

It wasn’t just the way that he stood: feet touching with legs pressed together from calf to thigh, shoulders down and back with a slight curve forward to his spine—but not too too much—fingers slightly splayed up and out with a careful angle to his wrists.

It wasn’t just the way he was dressed: a flowy white blouse with flowery accents, a lower, scooping neckline revealing absolutely nothing, as he had nothing to reveal, of course. A skirt, not a kilt, but a lady’s skirt, short and tiered, so it puffed up around his thighs. They were the perfect length to show just the slightest strip of bare skin, before it was hidden away again by thigh highs striped white and blue.

All from the woman’s section, of course.

And the most fucked up thing was that no one asked, not the cashier, not passer-bys, no one.

Because when he dressed up like this, he was so convincingly feminine that it almost deceived Damien at times. And he’d seen his literal dick, for fuck’s sake.

It was a weird hobby, a weird way to express oneself as a male, for sure. But looking back, it almost made sense, like he should’ve seen it coming. He’d always been soft-spoken and empathetic, and weird in the way he dressed and talked, stuck out like a sore thumb in shorts and pink socks the first time they met. And his wardrobe only got more and more odd from there.

But Damien must admit—as much as he does find it peculiar and doesn’t imagine he’ll ever truly understand his reasonings, and is somewhat glad to have moved to a city far away from South Park, so none of their childhood friends can make fun of him for walking around with a boyfriend with such an... effeminate hobby—he’s also quite pleased that Pip cross-dresses.

He does a damn good job of it, as aforementioned. Could trick anyone if he really wanted to, not that he really seems to. It’s more of a coincidence for him. No, Damien thinks it’s less of an act of purposeful deception, and more that he simply likes to look that way.

And, perhaps, be treated like a girl.

“It’s just,” Damien lets out an anxious breath of a chuckle, “I can’t believe you wore all this while we went out shopping for an entire hour.”

“Oh,” Pip giggles back, going to sit on the couch and mess with the pleating of his skirt. “Is that a bad thing?”

“No, no, not at all! Actually, I quite liked it,” Damien says, not even sure of what he’s saying, as he sits beside his boyfriend.

“Is that right?” he asks in his cheerful British accent, leaning closer to Damien, allowing him to see his soft eye makeup, black liner and pale pink lips, up close and personal. It certainly does accentuate his features, that’s for sure.

“I mean, I just think it’s neat, y’know, that you can do that. That no one even knows, you do such a good job of... acting like a girl, I guess.”

“Hm?” Pip nods.

“Takes a lot of balls.”

“Oh, that’s a good one,” Pip laughs.

But then the blonde shifts, scooting ever-nearer to the other until their hips meet, bodies flushed although there’s plenty of room left on the couch.

“But I meant, do  _ you _ like seeing me, dressed up like this?” he smiles as Damien looks down, his pastel painted nails running over Damien’s shoulders, sliding to his collar bone. “Does being out in public add anything to it, perhaps?” he giggles, shifting his thigh as something hard presses against Damien’s hip.

Damien almost couldn’t believe the filthy things such an angelic-looking creature was saying, doing.

But then he remembered it was Pip, and beneath that innocent appearance, was a tried and true slut. Of course he got off on this, at least half the time.

Damien grins back to him, moving his own hands down to Pip’s thin waist, then to the edge of his blouse to feel the soft skin beneath. “Well, I wasn’t really thinking that, if I’m being honest. But knowing now that that’s what  _ you _ were thinking...”

Damien sighs, pulling Pip’s shirt up and off, leaving the rest of his smooth body utterly exposed, eyes pin-pointing on his nipples, pierced with tiny but noticeable jewellery-like studs. “God, you’re such a whore.”

And just like that, Pip is suddenly pushed and pulled like some sort of martial arts move, all the way across the couch until he gets his bearings, finding himself strewn across the arm of the couch, ass high in the air and facing Damien.

And before he can ask what he’s doing, he lets out a yelp of pain, as the soft flesh of his round ass immediately reddens under a broad hand.

But then that yelp changes to a moan mid-way through, as Pip arches his back into the position, into his touch, pressing his bare chest to the velvet of the couch as he shakes his hips in a gesture that could only mean  _ more. _

Damien readily supplies, punishing his little harlot for being such a brazen slut—and out in public, too!

He lands moderate blows against the soft expanse of his ass cheek, switching from the right to the left every other time, to make it fair. The other hand lifts his skirt, grabs his hip to keep him steady as he keeps sliding forward with the force of his spanks, otherwise. He’s wearing white panties, which hide part of his ass to begin with, but slowly with the force and his struggling, pinch in between and press into his taint, his hard cock beneath just barely staying trapped inside of them, somehow.

But then Damien notices something.

“Oh,” he mutters, slapping his hand against him one more time for good measure, “are you kidding me?”

“Wh-what?” Pip sputters, breathless, tears in his eyes as he looks back. As though he doesn’t already know.

So Damien pushes his panties aside to manoeuvre his fingers into the space, landing directly on his hole.

But instead of entering him as he normally would, he’s met with something blocking him.

A metal anal plug. That he’d had inside him. This entire time.

“God, Pip,” Damien groans, feeling his own cock throbbing at the thought, as he moves to twist the base of it, drawing desperate cries from the other, “you really are going straight to hell, aren’t you? Jesus, I almost don’t understand, how in the world could someone wear something like  _ this,” _ he presses it deep into his hole as he can, ignoring the loud whine, “underneath all  _ that?” _

Damien repositions himself, the couch shifting under his weight, and suddenly, Pip’s met with a new kind of pleasure.

Not just in his ass as the plug is rotated and pulled and fucked back into him with a ruthless vigour, but in his cock, as he feels something equally hard and warm slide against the underside of his prick, just the thinnest layer of silk away from touching him directly.

A small but unmistakable extra bit of tortuously wonderful sensation is added by the piercing at the tip of Damien’s cock head, digging into the panties and grinding against his prick in an awful, amazing way.

It’s unfortunate that he’s so small that the entirety of his prick—leaking cock head and all—can stay straining within the confines of his panties. Otherwise, this would probably feel as amazing as it does to Damien, as he fucks Pip just like he would if he were penetrating him for real, but just a little lower, sliding between his thighs highs and against his panties, feeling the twitching of Pip’s cocklet with every thrust against him, every drag of the plug over his prostate.

“P-please, D-Damien,” Pip gasps, gripping the edge of the couch for dear life as Damien thrusts hard between his thighs. He’s giving him so much pleasure and pain already, but he wants more,  _ needs even more. _

“What is it, slut? You want me to fuck you, right here?” Damien grunts, shoving the metal plug, hot with body heat and friction, right back into his gaping hole.

Pip nods fervently, so he can’t miss it from his position above him, still frotting hard between his legs, pre-cum smeared all over his thigh highs, panties, skirt, some of Pip’s own wetting the front of his panties. There’d certainly be a lot of laundry later.

But now, Damien decides to have some mercy on his “girl”friend, so fucks once more, hard against his prick to make him cry out, then slides out all the way.

And the moment his cock is freed from the warmth between Pip’s wonderful thighs, he pulls the plug from his ass, tossing it somewhere behind them, and shoves right back inside him.

A cock buried inside his tight ass, properly, this time. Just as nature intended.

Pip cries out loudly in utter delight, nearly cumming just by being penetrated by such a thick, long cock—so much better than that little plug that had been shifting inside of him at all the shops and bumps of the car—but he’s barely able to hold on.

With all the frottage and foreplay, it’s no surprise that they’re already both sweating and panting like they’d done a marathon, depleted stamina meaning they don’t have much time left before they meet their ends.

So Damien makes it count, moving his hands from Pip’s curvy hips and up to his naked waist, feeling an odd satisfaction at the fact that his fingers can nearly meet, wrapped around his middle. But then he continues up as he fucks hard and deep inside him, world all heat and pleasure as he’s ready to cum any second inside of his tight, wet hole.

His fingers stop at the peak of Pip’s chest, grinding against the couch with every rough thrust. He circles around his nipples, hard as diamonds and pierced with a similar gem, until he begins pinching them, drinking in the squeals and moans he gets as a reward.

“You really are gorgeous, you know that?” Damien somehow manages to whisper into Pip’s ear, his gruff voice sending shivers up his spine as he ploughs right back into him, the piercing of his fat cock head hitting against his prostate in a way that makes him see stars and scream out loud.

“Fuck, you’re just so-so beautiful, and pretty, and nice and wonderful,” he huffs, the growing randomness of his shortening thrusts a sure sign to Pip he was about to cum—good thing, too, because he was about to cream his panties any damn millisecond now.

“I almost forget you’re a guy sometimes, you know that? Not until I get home and fuck you  _ just,” _ he thrusts,  _ “like,” _ again,  _ “this!” _

And with that, he cums, hot and wet as he fills Pip’s hole with all of his cock and semen, fingers pulling at his nipples harder than he ever has.

And just like that, as he’s filled with seed, Pip cums himself, most of his load staying trapped inside his panties still clinging to his hips, but some of it overflowing enough to leak from the fabric, dripping down and onto the couch as he shakes with the sheer force of his orgasm.

Pip’s knees finally give out, collapsing to lay on the couch and desperately try to catch his breath. Somehow, Damien stays inside him throughout the entire transition, so he’s lying flat on his back, which only makes it that much harder to breathe.

But he honestly wouldn’t prefer it any other way, he thinks with a smile, turning his head to give Damien a sweet kiss.

“You really think I’m all those things, do you?” he giggles giddily, more than delighted at Damien’s instant blushing.

“Oh, it’s okay, love,” Pip purrs, running a thumb beneath Damien’s chin lovingly, “I think you’re amazing and strong and wonderful, too. And I adore your tattoos.”

“Oh, shut up already,” Damien groans, tugging one more time on the piercings of his nipples.

And as he cries out and squeezes his thighs and ass around his cock on instinct, Damien grins one more time.

Sure, it might be weird, but having a cross-dressing slut of a boyfriend  _ certainly _ had its perks.

**Author's Note:**

> * * *
> 
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> 
> Thanks for reading! Ugh, I do love writing this pairing and sort of alternative fashion/lifestyle an awful lot, so I hope someone enjoyed it as much as I did writing it, hehe!


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